We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$2,730
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$95-$1,140
Sailboats
Set sail with these traditional wind-powered boats
$155-$2,535
Fishing Charters
Let a captain do the driving while you do the fishing
$100-$1,090
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$1,145
Kayaks
Who says you need a motor to have fun on the water?
$30-$3,285
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$95-$4,470
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$120-$150
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$630
Diving
Explore the ocean depths with trained boat operators
$850
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$115
GS
Genevieve
Private San Juan Bay Cruise 37' Sailboat
I booked with Captain Luis for my sister’s 30th birthday trip, and we all had the best experience! There were 4 of us in San Juan for a long weekend and this was the highlight of our trip. We felt safe, welcome, and taken care of the whole ride - the captain brought refreshments including Sangria that his wife had made which we all loved. He sailed us around and anchored at a beautiful spot to jump in and swim which was so fun. I highly recommend!
SA
Samuel
Private San Juan Bay Cruise 37' Sailboat
Captain Luis and Andrea are the real deal! We spent so much time figuring out the best sailing experience and we couldn’t have been more lucky to have found the of them and this sailing experience from San Juan bay watching the sunset and seeing the beauty of the fort and gorgeous old San Juan!!! They are so seasoned and know the waters so well that our ride was just a peaceful incredible magical ride and was the highlight of our trip!!! Trust me, stop looking and hurry and book. They are worth it and the experience will be for a lifetime!!! Thank you again guys for the beautiful evening for my fiance and I
SD
Sarah
Private San Juan Bay Cruise 37' Sailboat
My husband, 2 small kids, and I went on a morning 4 hour sail with Luis and Andrea. Luis and Andrea were kind and always looking out for us enjoying our experience. Our kids had lots of fun and my husband and I were able to relax and enjoy the scenery. I 100% recommend booking a cruise with Captain Luis!
KB
Katherin
Private San Juan Bay Cruise 37' Sailboat
Don’t second guess it. Just book it. Luis and Andrea were great! They were helpful before and during the trip. We had gone for a relaxing trip for my cousin’s bachelorette. They offered a charcuterie tray and some Sangria. I would definitely book again, on another trip to PR (:
RB
Rachel
Private San Juan Bay Cruise 37' Sailboat
This was the highlight of our trip to Puerto Rico. Captain Luis was so communicative and friendly from booking to the end of the trip. I booked this experience for a friends bachelorette and it was her favorite part. He provided sangria and a small charcuterie board which was delicious. We asked to swim and he anchored for about an hour for us to enjoy the beautiful waters. Safety was a priority which we appreciated. He and his first mate Andrea were amazing. Andrea is incredible. Captain Luis even danced salsa for us hahaha.
CF
Connie
Private San Juan Bay Cruise 37' Sailboat
I had my bachelorette party with 6 women in Capt Luis' boat. I wanted a relaxing sailing experience in San Juan, as well as have the option to jump into the water, if we wanted. This was perfect for us. The water was very calm when we went. Capt Luis was good at listening to what the customer wants, and he adjusted to my preferred timeline, and I really liked that. He was very responsive via text, and email. And I would say, after doing my research and messaging a lot of boat companies, his pricing was the most reasonable and he was also the most responsive. My girls and I had a great time! The only thing I would give others a heads up is that the complimentary tapas and drinks that come with a 3-hour booking, is minimal. So if you and your guests are hungry and thirsty bunch, it is best to bring more of your own tapas/drinks. Regardless, I would still book him again as he was very professional and had great communication skills. It was an easy transaction despite my fickle mind.
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
September 05, 2023
Read Article
February 18, 2022
Read Article
December 13, 2021
Read Article
June 18, 2021
Read Article
December 26, 2019
Read Article
December 18, 2019
Read Article